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MedKoo Cat#: 598704 | Name: Levamlodipine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Levamlodipine is a dihydropyridine calcium channel blocker used to treat angina and hypertension.

Chemical Structure

Levamlodipine
CAS#103129-82-4

Theoretical Analysis

MedKoo Cat#: 598704

Name: Levamlodipine

CAS#: 103129-82-4

Chemical Formula: C20H25ClN2O5

Exact Mass: 408.1452

Molecular Weight: 408.88

Elemental Analysis: C, 58.75; H, 6.16; Cl, 8.67; N, 6.85; O, 19.56

Price and Availability

Size Price Availability Quantity
1g USD 250.00 2 Weeks
5g USD 550.00 2 Weeks
10g USD 850.00 2 Weeks
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Synonym
Levamlodipine; S-Amlodipine;
IUPAC/Chemical Name
3-ethyl 5-methyl (S)-2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate
InChi Key
HTIQEAQVCYTUBX-KRWDZBQOSA-N
InChi Code
InChI=1S/C20H25ClN2O5/c1-4-28-20(25)18-15(11-27-10-9-22)23-12(2)16(19(24)26-3)17(18)13-7-5-6-8-14(13)21/h5-8,17,23H,4,9-11,22H2,1-3H3/t17-/m0/s1
SMILES Code
O=C(C1=C(COCCN)NC(C)=C(C(OC)=O)[C@@H]1C2=CC=CC=C2Cl)OCC
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Levamlodipine ((S)-Amlodipine) is a powerful dihydropyridine calcium channel blocker, possessing vasodilation properties and used in the treatment of hypertension and angina.
In vitro activity:
In human umbilical vein endothelial cells (HUVECs), miR-155, RANK, and RANKL levels were significantly decreased, while OPG mRNA levels were significantly increased in the S-amlodipine group. S-amlodipine significantly inhibited RANKL expression and NF-κB phosphorylation, and there were no significant differences in response to the NF-κB inhibitor (Bay110785). Referemce: Biomed Pharmacother. 2019 Jun;114:108799. https://pubmed.ncbi.nlm.nih.gov/30951948/
In vivo activity:
Furthermore, vehicle-treated mice revealed reduced phospho-CaMKII (Thr286) levels in the hippocampus, which can be partially restored by levamlodipine besylate (0.1 mg/kg and 0.5 mg/kg) treatment. Reference: Sci Rep. 2019 Dec 3;9(1):18248. https://pubmed.ncbi.nlm.nih.gov/31796756/
Solvent mg/mL mM comments
Solubility
DMSO 91.0 222.56
Ethanol 82.0 200.55
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 408.88 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Yang J, Si D, Zhao Y, He C, Yang P. S-amlodipine improves endothelial dysfunction via the RANK/RANKL/OPG system by regulating microRNA-155 in hypertension. Biomed Pharmacother. 2019 Jun;114:108799. doi: 10.1016/j.biopha.2019.108799. Epub 2019 Apr 2. PMID: 30951948. 2. Wang RX, Jiang WP, Li XR, Lai LH. Effects of (S)-amlodipine and (R)-amlodipine on L-type calcium channel current of rat ventricular myocytes and cytosolic calcium of aortic smooth muscle cells. Pharmazie. 2008 Jun;63(6):470-4. PMID: 18604992. 3. Yao KX, Lyu H, Liao MH, Yang L, Gao YP, Liu QB, Wang CK, Lu YM, Jiang GJ, Han F, Wang P. Effect of low-dose Levamlodipine Besylate in the treatment of vascular dementia. Sci Rep. 2019 Dec 3;9(1):18248. doi: 10.1038/s41598-019-47868-0. PMID: 31796756; PMCID: PMC6890753. 4. Suchanova B, Sispera L, Wsol V. Liquid chromatography-tandem mass spectrometry in chiral study of amlodipine biotransformation in rat hepatocytes. Anal Chim Acta. 2006 Jul 28;573-574:273-83. doi: 10.1016/j.aca.2006.05.065. Epub 2006 Jun 2. PMID: 17723534.
In vitro protocol:
1. Yang J, Si D, Zhao Y, He C, Yang P. S-amlodipine improves endothelial dysfunction via the RANK/RANKL/OPG system by regulating microRNA-155 in hypertension. Biomed Pharmacother. 2019 Jun;114:108799. doi: 10.1016/j.biopha.2019.108799. Epub 2019 Apr 2. PMID: 30951948. 2. Wang RX, Jiang WP, Li XR, Lai LH. Effects of (S)-amlodipine and (R)-amlodipine on L-type calcium channel current of rat ventricular myocytes and cytosolic calcium of aortic smooth muscle cells. Pharmazie. 2008 Jun;63(6):470-4. PMID: 18604992.
In vivo protocol:
1. Yao KX, Lyu H, Liao MH, Yang L, Gao YP, Liu QB, Wang CK, Lu YM, Jiang GJ, Han F, Wang P. Effect of low-dose Levamlodipine Besylate in the treatment of vascular dementia. Sci Rep. 2019 Dec 3;9(1):18248. doi: 10.1038/s41598-019-47868-0. PMID: 31796756; PMCID: PMC6890753. 2. Suchanova B, Sispera L, Wsol V. Liquid chromatography-tandem mass spectrometry in chiral study of amlodipine biotransformation in rat hepatocytes. Anal Chim Acta. 2006 Jul 28;573-574:273-83. doi: 10.1016/j.aca.2006.05.065. Epub 2006 Jun 2. PMID: 17723534.
1: Qi Y, Zhang X. Determination of enantiomeric impurity of levamlodipine besylate bulk drug by capillary electrophoresis using carboxymethyl-β-cyclodextrin. Cell Biochem Biophys. 2014 Dec;70(3):1633-7. doi: 10.1007/s12013-014-0106-2. PubMed PMID: 25269770. 2: Yang YL, Yu LT, Wu ZT, Yu JG, Zhang JM, Chen QH, Bao YC, Liu JG. Synergic effects of levamlodipine and bisoprolol on blood pressure reduction and organ protection in spontaneously hypertensive rats. CNS Neurosci Ther. 2012 Jun;18(6):471-4. doi: 10.1111/j.1755-5949.2012.00323.x. PubMed PMID: 22672299. 3: Gui H, Guo YF, Liu X, Zhang JM, Yang YL, Huang GZ, Liu JG. Effects of combination therapy with levamlodipine and bisoprolol on stroke in rats. CNS Neurosci Ther. 2013 Mar;19(3):178-82. doi: 10.1111/cns.12057. PubMed PMID: 23441690. 4: Xiao WY, Ning N, Tan MH, Jiang XS, Zhou L, Liu L, Yi D, Wei P. Effects of antihypertensive drugs losartan and levamlodipine besylate on insulin resistance in patients with essential hypertension combined with isolated impaired fasting glucose. Hypertens Res. 2016 May;39(5):321-6. doi: 10.1038/hr.2015.155. Epub 2016 Jan 14. PubMed PMID: 26763851. 5: Liu Z, Zheng X, Yang X, Wang E, Wang J. Affinity and specificity of levamlodipine-human serum albumin interactions: insights into its carrier function. Biophys J. 2009 May 20;96(10):3917-25. doi: 10.1016/j.bpj.2008.12.3965. PubMed PMID: 19450464; PubMed Central PMCID: PMC2712192. 6: Xiao H, Fu X, Liang S, Li Y, Bao JJ, Zhang Y. An approach to the determination of the enantiomeric excess at the extreme case by capillary electrophoresis. J Chromatogr A. 2015 Aug 21;1408:250-4. doi: 10.1016/j.chroma.2015.07.006. Epub 2015 Jul 4. PubMed PMID: 26166294. 7: Jain R, Sinha A, Khan AL. Polyaniline-graphene oxide nanocomposite sensor for quantification of calcium channel blocker levamlodipine. Mater Sci Eng C Mater Biol Appl. 2016 Aug 1;65:205-14. doi: 10.1016/j.msec.2016.03.115. Epub 2016 Apr 11. PubMed PMID: 27157745. 8: Rong H, Tan M. [Effect of probucol on serum malondialdehyde and superoxide dismutase in patients with primary hypertension]. Zhong Nan Da Xue Xue Bao Yi Xue Ban. 2012 May;37(5):458-62. doi: 10.3969/j.issn.1672-7347.2012.05.005. Chinese. PubMed PMID: 22659656. 9: Xu SM, Wang YL, Li D, Li XM, Li D, Xu PS. Randomized, two-way crossover bioequivalence study of levamlodipine besylate tablets in healthy Chinese subjects. Int J Clin Pharmacol Ther. 2017 Oct;55(10):818-824. doi: 10.5414/CP202998. PubMed PMID: 28619129. 10: Wang Q, Zhao T, Mi BT, Zhang YL, Wei R, Tong HL, Wu M. Primary Colonic Angiosarcoma Seen in a Patient on Calcium Channel Blocker: A Case Report with Summary Analysis of 32 Other Cases from the Literature. Am J Case Rep. 2018 Mar 7;19:254-261. PubMed PMID: 29511155; PubMed Central PMCID: PMC5850845.